


The Sexy Mouthful and the Sexy Assful

by LavenderNomad



Series: A First Time For Everything [2]
Category: Supernatural
Genre: Anal Sex, F/M, Female organs, Multi, POV Second Person, She/her pronouns, Spitroasting, Use birth control irl, Vaginal Sex, unprotected sex
Language: English
Status: Completed
Published: 2016-07-26
Updated: 2016-07-26
Packaged: 2018-07-26 22:43:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,698
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7593055
Author URL: https://archiveofourown.org/users/LavenderNomad/pseuds/LavenderNomad
Summary: <blockquote class="userstuff">
              <p>Dean and Sam show you some of the other firsts you can try.</p>
            </blockquote>





	The Sexy Mouthful and the Sexy Assful

You woke up to the sounds of hushed arguing that morning. As you turn, whining a little, the sounds stop and you fumble through the sleepy haze to figure out what was going on. The sounds stop immediately and the bed around you sinks slightly. You blink the sleep from your eyes and are greeted by the smiling, charming faces of Sam and Dean Winchester. Almost yelping, you sit up, clutching the sheet to your chest. “H-hey!”

Dean chuckles at you from the foot of the bed as Sam kisses your cheek. “Good morning,” he whispers in your ear. Your face heats up as you remember last night, and you squeak pulling the covers up to your cheek as the older Winchester smiles predatorily at you.

“Get dressed before I collect my promise early,” he says, throwing you some clothes.

–

The day time was spent at a diner, newspapers spread out around the three of you in a booth. Your skin tingled with every movement, your heart had pounded wildly in your ears all morning. You were completely unable to focus on the narrowed list of cases at hand—a mysterious bright light in Pawnee, Indiana followed by what appeared to be horse shoes leading nowhere, an antique’s roadshow with hosts dieing every time they passed through Iowa, violent disappearances in Henderson, Las Vegas… no, you were much more focused on Dean’s hand on your thigh under the table, rubbing circles dangerously close to your crotch. Sam showed his affection by reaching across the table every so often to trace a shape on your hand while smiling shyly before withdrawing to type some more.

You absently suck on your spoon after eating some pie and flush hot as both boys stared at your lips. You gulp, cough and lower your eyes. “Uh—yeah, so I dunno about that horse thing… doesn’t sound so serious, right?” Even after last night, you couldn’t help but be completely useless at flirting. Dean squeezes your thigh, sending shooting pleasure up your spine and you shiver.

“Yeah,” Sam finally pulls his eyes away from you. “I guess one of the regional directors or something out there goes overboard every year for some horse festival. It looks like this might just be an advertising stunt, not really our stuff.”  
“Horse festival?” Dean snorts. You hide your flustered face in a cup of strong coffee. The rare moments neither of them were focused on you gave you a chance to breathe.

“I’m going to the restroom,” You mutter, standing up. You try to step confidently away, but can feel the burn of their eyes on your back. In the bathroom you examine yourself. Your face had a slight sheen, probably due to the slight discomfort of your situation, and you wipe at it.

You stare at your reflection. You can’t wait to just get back to the hotel. 

–  
Dean had kept good on his word.

Having almost finished your shower, you had turned to see Dean encase you in his arms, pressing you against the cold linoleum of the tub. His lips sought yours, searing your skin with desire, your actions still awkwardly coordinating to his fluid, experienced ones. Eyes closed, you let the sensations of his rough hands sliding down your sides under the water overwhelm you; the water seemed to drag the sensation along. You moan, your core heating up almost immediately as you wrap your arms around his neck, tasting him, water filling you mouths to be dribbled out as his tongue brushed against yours. The kiss was passionate but gentle. You shivered at the chill against your back, which brought a deep, desiring growl from him and he released your lips in favor of your pulse.

“D-Dean…” Your voice is an unrecognizable, throaty whisper. You clutch his shoulders, before tracing his name out with your index fingers.

He sucks gently, teething it as his thumb massage your hips. His fingernails trace your buttocks, and you moan, tingles racing up and down your back at the sensation. Seeming to like the reaction, Dean fully grasps your bottom, a cheek in each palm, and begins massaging, almost lifting your off the bathroom floor. You gasp, eyes rolling to the back of your head as the sweet pain-pleasure rushes to your core, and you are sure you are wet. 

“Oh god—“ He swallows your words, spreading your buttcheeks apart; his kiss is more needy, his hard-on pressing against your thighs. He leans back, his green eyes darkened with lust, his face stoic and focused on yours as he continued squeezing and rubbing you. You bite your lip at seeing him with his hair dampened against his forehead, whimpering as he slides a finger down the crack, tickling you in a way you hadn’t imagined. Dean gulps visibly, leaning forward to brush his lips to your ears.

“Sam might’ve been first here…” Dean grinds against your outer lips. “… But I can be a first too.” His voice is a low, lusty growl, thick and electrifying. You gulp and nod.

He kisses you in approval, sliding you up against the wall; those strong arms can lift. He slowly slides your pussy onto his length, the water hindering and washing away your wetness slightly but he is steady and patient. You, on the other hand, savor the slight stretch and pulling of your skin, the pain blending into pure desire for him. Only when he is completely sheathed in you, do you notice his fingers tickling the puckered skin of your anus. You whimper in pleasure; the stretching of your vaginal walls and the fingers gently stretching ever so slightly—it was so good and you dance on your tip toes, struggling to find footing as you hold him tight to you. He leans forward so his ankles are anchored against the side of the tub, and he gives an experimental thrust. He groans your name. “ _Fuck,_ you feel so good, fuck fuck.”

 

Dean’s beautiful hazel eyes gaze at you, drops of water running down his face, catching in his lashes. He looks so intently at you, so intense and focused and you nearly lose your breath. His short blonde hair is colored brown and wetted against his forehead and he leans forward to kiss you, to communicate. His eyebrows furrowed as he works against you, rotating his hips within your hot, wet pussy. He presses his palms next to your head, and you keep your legs wrapped around his waist as he rolls his hips into yours. You sigh his name over, and over; his passionate thrusts are measured, slow, controlled, as though he wants to savor this moment. You open your eyes to see him gazing at you, that same intense look on and you wrap your hands in his hair to pull him to your lips. His response is to grind his hips against yours, burying himself deep into you. He massages your sides as you whimper, struggling against him, wanting more friction. He pulses his thighs, twitching ever so slightly within you, and he begins a tracing a circle, his cock pulling out ever so slightly only to slowly press askew back in.

“Deeeean,” you sigh, “need you, need more-“

“Say it again,” he demands, throat hoarse with restraint. You arch your back into him, successfully pulling him in ever so slightly.

“Dean, I want more.”

He begins rolling his back, thrusting into you over and over without really ever leaving your warmth, twisting his hips to stretch every part of your core, every corner brushed and pushed against. The water begins to feel so hot as tension stretches across your skin, your bodies slick with water. You move your hands, one to hold the back of his neck, the other feeling, grasping every inch of him, his muscles rippling in approval. He sucks below your ear, and your eyes close. The warmth of his body and the water pressing against you, the feeling of his strong legs between your legs, the incessant pounding, the intimacy of his muscles pressing against the softness of your flesh—

Your orgasm washes over you, the water massaging the wave throughout your body, and you uncontrollably clench around him over and over again. Dean groans, pressing tight against you so you don’t push him out of you. He takes a long shuddering breath, pausing in his movements as you swirl down lazily back into your body, not realizing he is licking a sensitive spot below your ear—probably a hickey—and you are calling his name, your voice winding down to a reverent whisper, a prayer to his name. Still inside you, Dean shuts off the water and carefully holding your waist, steps out. 

“What are you doing, Dean?” He doesn’t answer you, simply rolling his hips up in answer and you cling to him, clenching your inner walls against him. He grits his teeth, opening the door. He steps out, throwing you onto the bed next to Sam, who is rubbing himself through his shorts, his brown hair already dry from his own shower. His neck muscles are strained, the loose tshirt dipping low enough to brush his collar. His shorts are tented, and he rubs the edge.

“You sound so good, echoing around in there,” the younger brother tells you as he pulls you to him, kissing him. His kiss is rough, desperate—he wants to taste you; he too has wanted you all day. You hear the vague sounds of Dean zipping and shuffling around in his bag but you are experimentally sliding a hand up Sam’s shirts, feeling the hard muscles, appreciating him. He nods, and you graze your finger nails against them before you break away, shyly moving down his lap. Sam is transfixed on you as you slip your fingerpads under the waistband of his shorts, snapping them. You lay between his calves, your thighs on the edge of the bed. Propping yourself up on your elbows, you notice Sam’s eyes on your cleavage and you teasingly press your arms tighter together.

“Looks like our baby girl is getting forward, huh, Sammy?” Dean’s low voice comes from behind you and you shoot your head to look at him. He has a bottle of something clutched in his fast and you shiver—partially from the cold on your wet skin, partially from the rippling of his body, his broad chest narrowing into muscled hips, into strong thighs. His cock stands hard and proud, dripping.

“Go on, keep playing with Sammy,” Dean encourages. You turn back to Sam, letting go of his waistband again, his groan sending feminine pride through you. You trace the shape of him through the cotton fabric of his shorts, tickling the side of his balls with your nails.

Dean spreads your buttcheeks and you gasp. He drips something cold against you, the flesh of your cheeks shivering. It slides down, slowly heating up against your skin, and you bite your lip, turning slightly to watch as the older brother, eyes watching your backside, slides his thumbs around the sensitive flesh, pulling it open. Sam tilts your chin to him, his hand having impatiently pulled his own cock out of its restraint, his scent clean but undeniably him.

You move up slightly biting your lip, gazing at it, before you look up at him. He nods and you guide his cock into your mouth, and you wrap your lips just below the head, watching to gauge his reaction as you slide your tongue around the head. His precum is mostly tasteless, and you swallow it down. He groans, sliding a hand to pet your hair, closing his green eyes.

You whimper as you feel Dean slide a finger into your tight, pucked anus and you instinctively try to move away only to be held by his forearm. He progresses and you wince slightly; he pauses. You breathe through your nose and swallow some more of Sam’s cock, the head now at the back of your tongue and in the same breath, Dean has pushed his index to his knuckle.

The sensation is completely new to you; he was stretching you, and as he gently pressed his finger towards your stomach, your pussy wall fluttered. You nod and moan in approval, the humming noise encasing Sam’s hardness. You swallow your gag reflex down and simultaneously swallow even more of him. Your cheeks bulging, you struggle to gaze up at him, only to be answered by Sam’s lusty, “Oh fuck yeah.”

Dean is gently feeling around your anus, tickling your insides and you wriggle your hips as he presses down again, the pressure feeling similar to his cock against your womb. He chuckles, spreading your cheeks apart to slide another finger in—you stiffen at first but relax, as he moves past that first ring of muscles to slide his middle finger along his pointer. You swallow, somehow slowly taking more of Sam down your throat and when you are nose to his bush of thick hair, you simply continue the swallow motion, working your throat around him. Although slightly uncomfortable, the feeling of his hot, thick cock in your throat felt punishingly good, and his warm skin was velvety soft against your lips.

Your eyes slide shut as Dean slides his fingers out then slides them back in to the hilt of his hand, excrutiatingly slow. He speeds up just so slightly, your back arching as he manages to press against the thin wall separating your pussy and ass, the sensation vibrating that thin wall. You slide your face off Sam’s dick only to slide it back in, in and out, as Dean matches your pace. Your eyes are squeezed shut only flying open as Dean pauses to force a third finger in. Your eyes roll up and Sam pulls your head up so you are just sucking the head. “Look at me, baby, fuck.”

You comply, meeting his aroused gaze, before you grasp the base of his cock, your throat needing a break. You pump up and down, your saliva and his precum providing sufficient lubricant and you lick your lips, watching the skin gather around the base of his head before sliding down with your hand. You lick around the base of the head, Dean’s fingers in your ass providing a hum of pleasure and pain; he fans them so slightly, and you groan at the stretching sensation, releasing Sam’s penis from your lips and putting your forehead on his thigh. You can’t focus on the sensations and sucking him so you wrap your palm tigher, pumping harder up and down.

Dean’s hands release you and you pause, looking back. He is rubbing his cock, spreading something shiny over it and you bite your lip, apprehension breaking through the cloud of lust. Despite the thickness of his three fingers, his cock still looked bigger. You stop your ministrations on Sam as he pulls your hand off his cock and you look up at him.

“Watch me, babe,” He whispers, his concern shining through hooded eyes. You nod.

“You ready?” Dean says behind you and you nod. He uses one hand to spread your ass and you almost jump feeling the hot head of his cock press against the puckered skin. You breathe and relax, and he slowly slides the tip of his head, only to almost slip back out on the lube, the muscles of your butt pressing him out. “Fuck, you’re still so tight,” He says, somewhat frustrated. You reach one hand back to spread the other cheek and both men voice their approval.

With your help, he manages to slide his cock in, inch by painfully pleasurable inch. You grit your teeth slightly, calming as Sam brushes your hair, holding your hand. You rest your head on lower stomach a second before pushing down and back onto Dean. He gasps in surprise as he is suddenly pushed past that tight ring of muscles and is sheathed fully within your asshole.

“Shit, you’re really hot here,” He can barely get out. Dean’s hands clench your hips, trying to keep himself from shoving himself wildly in and out.

Breathing, you distract yourself by taking as much of Sam into your mouth without warning, the stretching of your anus and throat becoming mixed, the pleasure and pain also mixing. Sam’s hands shoot to your hair.

The pain dulls to a slight hum, and you nod, and begin moving your jaw up and down Sam’s cock, only pausing to give your throat a break and suck hard on the head; Dean slides out slightly, to thrust back in, his length pressing that same spot in your ass. Pleasure shoots through you, and you press needily back against him. You slide one hand to the demanding nub of your clit, the other still grasping the younger Winchester’s dick for support. You slide the nub between your fingers and rub, feeling Dean become more confident in his thrusting. He again never pulls fully out, just enough to gain some friction. His thighs are pressed tight against yours, his hands holding your waist tight. You spit Sam’s cock out a second to look behind you, and rub yourself harder as you see him. His eyes are closed reverently, head tilted up slightly; droplets of water trace down his skin, his muscles taught with motion. He opens his eyes to catch your gaze and smirks, giving a particularly hard thrust you feel in your pussy and you slip one finger into your warmth, turning to look at the younger brother. His eyes are dark, his muscles stretched, light glistening on his skin. His fingers rub the back of your head, encouraging you to his member again, which you take once more into your mouth. You slide another finger into your pussy, lazily tickling yourself as Sam gently lets one thrust into your mouth before restraining himself. You bob up and down, only taking as much as you can into just your mouth, and intermittently squeeze with your free hand. You half watch him and his jaw tighten and tic at your ministrations, your name falling from his lips over and over.

Dean presses your hips down slightly to better access you, his cock sliding easily in and out now; he stops when he is fully in you to roll his hips into you before picking his pace back up. His hips are slapping against your buttocks and as if on cue, he slides one hand from your hips to squeeze a cheek, almost too roughly and you moan. Your eyes are rolled to the back of your head, your finger desperately sliding in and out of your soaking pussy and against your clit, Dean’s dick making a sloshing noise as he begins to push in and out wildly. He leans over your, his cock angling down against that thin wall and his chest presses, warm, against your back.

“Fuck, I’m gonna fill this asshole up,” He mutters in your ear. You nod and moan, Sam’s dick vibrating in your mouth in response. “You want me to be the first to spill cum in here, hm, baby? You want me to be the first to fill it up to the brim?”  
His words are so hot, and you try to cry a response from around Sam’s cock, only succeeding in sliding your tongue against it. You thrust your fingers in and out of your pussy at the same pace as Dean’s thrusts, praying your arm didn’t grow too tired before you came, before that coil in your stomach broke.

Dean presses himself tight against you, twisting his hips in your ass before you feel his cock twitch; he rotates his hips sharply, loudly growling your name as he fills you up like he promised. He grasps your ass in his palms, his cock slowly deflating in your ass, but you are focused on your own orgasm. Sam thrusts gently into your mouth, one hand reaching beneath your face to cup at his balls. He holds them to him body, one hand behind your head, gently helping you move up and down, up and down. You let him fuck your mouth, pressing faster and hard against your clit, each movement bringing you ever so slightly closer and closer. Dean continues to massage your ass cheeks, and Sam’s huge, hot cock twitches slightly in your mouth. He cries your name as cums; he tries to keep his hips down but can’t help but shove his cock just slightly against the back of your throat as he comes, spurting into and filling your mouth with his bitter semen.

The taste, though strong and lingering and honestly quite gross, sends you over; it drips out your mouth, back onto his dick and your body lights up all over, your pussy clenching and unclenching. You shake gently as you come, sucking in a breath; their cum is inside you, inside your throat and ass, your own pussy juices sliding down your legs.

You collapse onto Sam’s lap, legs shaking violently. You take deep breaths, kissing the side of Sam’s slowly shrinking cock, cum sticking to your lips again. Dean finally pulls his fully released cock out of you and you whimper, feeling his semen slide out of you and down your thighs. He crawls up next to you, rough, calloused hand gently sliding up your back.

Once again, they manhandle you so you are spooned against Dean, this time facing Sam’s puppy eyes. He smiles almost sheepishly at you, touching your lips, pulling cum away. “Sorry about that.”

“It’s okay,” you mumble, before coughing, reaching into your mouth at something itchy. You come away with a long, brown hair and Sam blushes. “Well, I got your pubes down my throat too.”

“S-sorry!” He says, kissing you in apology.

Dean reaches an arm under you, lazily cupping your breasts. You whine, body too sensitive. He acquiesces, sliding it down to your waist as he presses his face into your hair. “How was that?” He says sleepily.

“You sexed me pretty good,” You respond, smiling. Sam leans his forehead against you.

“Good.”


End file.
